Any V16 will have a ridiculous front end. And the Cadillac Sixteens defined the genre for its entirety. The gorgeous and clearly ultra-plush proportions of the Cadillac V16 are best on the LWB 7-seater limo. The shorter cars are gorgeous and huge too, but just not as lovely and cartoon-y (in a good way).

The provenance of this particular car as a Special Body Order is a good clue to its famous owner: Joseph Kennedy, father of President John F. Kennedy and Hollywood tycoon. So not just a glitzy limo with scale to make you pale… but this very car was a Kennedy compound all-star.

1937 Cadillac V-16 Fleetwood Limousine

1937 Cadillac V-16 Seven-Passenger Limousine by Fleetwood

Body Style 5875. 185 bhp, 452 cu. in. OHV V-16 engine, three-speed manual synchromesh transmission, leaf-spring front axle, torque tube rear axle, and four-wheel power-assisted drum brakes. Wheelbase: 154 in.

• One of the last of the first-generation Cadillac V-16s built

• Exported in period to the United Kingdom; believed to have been used by Joseph P. Kennedy Sr.

• Formerly of the John Cuthill Sword Collection

• Largely original and matching numbers, with 22,000 believed actual miles

• CCCA Full Classic

Chassis number 5130347 was the third-from-last of the first generation Cadillac V-16s built and one of only 49 cars assembled in the original V-16’s last year of production. Of these, 24 were produced as the seven-passenger limousine by Fleetwood. Its fascinating original build sheet is a multi-page document, a copy of which accompanies the car, and it notes that the Cadillac was a “Special Body Order”; unfortunately, the specifics of this are long since lost.

The Cadillac has long been attributed to Joseph Kennedy Sr., the father of President John F. Kennedy, during his service as the United States Ambassador to the Court of St. James’s from January of 1938 until October of 1940. Recent investigation of the car’s build sheets by Cadillac historians Chris Cummings and Alan Merkel indicates that the car was diverted to New York in the third week of August 1937, as the second page is the newer form used on build sheets for 1938 and later Cadillacs. According to Cummings, the actual shipping ledger shows a date for this car of December 31, 1937, by which time the new forms would have been available. This was late in the same month in which Kennedy was named as Ambassador, and the bargain price involved in purchasing last year’s model would have appealed to his famous New England frugality. Thus, the car fits cleanly into the Kennedy legend.

That the car was indeed exported to England early in its life is without question, as it was registered in London as FXU 1. The original registration plates and special taillights fitted during its time in the country are still with the car today.

Later, the car made its way into the Scottish collection of John Cuthill Sword, a very early and prominent enthusiast, at whose landmark estate auction it was sold in 1962. It was eventually acquired by the well-known British dealer Charles Howard, from whom it was exported to North America in 1994. Since its arrival on these shores, the car was owned by Earl Hickman and Dennis Gibbs, of Texas, before being acquired in 2006 by its present owner, a well-known and respected collector of V-16 Cadillacs. In his ownership, it has been shown and enjoyed, and, appropriately, it appeared in the 2010 television miniseries The Kennedys.

The V-16 has been refinished in its original Black color but remains otherwise original, including surface-cracked leather for the front seat upholstery and excellent Weise Bedford Cord cloth for the rear seat upholstery. The paint shows minor cracking, checking, and blistering in stress areas, and the chrome trim is in largely original condition and shows its age without any damage. Importantly, the Cadillac is still fitted with the very rare “watch winder” hubcaps. The car was serviced last fall, including adjustment of the valve timing and idle speed. An RM Sotheby’s Specialist recently drove FXU 1 and reported that it starts and drives very well with excellent handling and power, as well as fully functional brakes and instrumentation.

It is accompanied by ownership and export documentation from through the years, including copies of the Sword catalogue entry, copies of the build sheets, and the aforementioned original London registration plates and British taillights.

This is a wonderfully original, well preserved, and happily storied automobile, with fine history as one of the last V-16s built; it has led a well-traveled existence—perhaps including use by the patriarch of America’s greatest political dynasty.